2-Fluoropyridine → 2-Methyl-1-(pyridin-2-yl)-1H-benzimidazole

HRID 50904

반응식

HRID 50904 반응식
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[H-].[Na+].F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>CC(N(C)C)=O>[CH3:1][C:2]1[N:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

참가 물질

5

반응물 3

HCID 97462-FluoropyridineHCID 119842-MethylbenzimidazoleHCID 24758Sodium hydride

생성물 1

HCID 227366432-Methyl-1-(pyridin-2-yl)-1H-benzimidazole수율 71.3%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매3회

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 2-methyl-1H-benzimidazole (6.61 g, 50 mmol) in dimethylacetamide (40 ml) at room temperature under a nitrogen atmosphere was added sodium hydride (2.40 g, 60 mmol) in portions during 15 min. At the point where the reaction mixture was too viscous to stir, the reaction was diluted with 100 ml of dimethylacetamide. After 50 min., a solution of 2-fluoropyridine (5.83 g, 60 mmol) in dimethylacetamide (30 ml) was added during 15 min. The resulting mixture was heated at 100° C. for 2 h and then to reflux for about 4 h. Volatiles were removed by evaporation under reduced pressure. The residue was dissolved into ethyl acetate (200 ml) and washed consecutively with water (3×100 ml) and brine (100 ml). The organic layer was dried (magnesium sulfate) and concentrated to dryness. Purification by column chromatography (silica gel, 300 g; n-hexane/ethyl acetate (17/3)) yielded 7.46 g (71%) of the titled compound as a light yellow liquid. 1H-NMR (CDCl3) δ: 8.72-8.67 (1H, m), 7.95 (1H, ddd, J=7.7, 7.7, 1.8 Hz), 7.78-7.74 (1H, m), 7.49-7.36 (3H, m), 7.32-7.20 (2H, m), 2.69 (3H, s).

후처리

  1. temperatureto reflux for about 4 h
  2. customVolatiles were removed by evaporation under reduced pressure
  3. dissolutionThe residue was dissolved into ethyl acetate (200 ml)
  4. washwashed consecutively with water (3×100 ml) and brine (100 ml)
  5. dry with materialThe organic layer was dried (magnesium sulfate)
  6. concentrationconcentrated to dryness
  7. customPurification by column chromatography (silica gel, 300 g; n-hexane/ethyl acetate (17/3))

출처 및 근거

ORD 기록
ord-e3afa1e531c442fe976e5b9318187d1d
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713482B2

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